A Word, Please: Knowing when to capitalize can be hard. Here are some basic rules

Does your Bostonian friend hail from the City of Boston or the city of Boston?

Before you answer, here’s a hint: It depends who’s asking.

I flunked this question on an editing quiz recently. I got it wrong even though I’ve spent decades — literal decades — getting paid to change City of Los Angeles to city of Los Angeles and City of Pasadena to city of Pasadena.

So what happened? I was editing according to Associated Press Stylebook rules and the quiz was in Chicago Manual of Style rules.

In AP style, which is followed by many news media and business organizations, the c is lowercase. I like that. After all, “city” isn’t part of the name. If you live in Boston, you don’t write City of Boston on the top left hand corner of envelopes when you send mail. The city name is Boston, period. But the Chicago Manual of Style, which is followed by book and magazine publishers, disagrees. If you’re following their style, City of Boston can be the way to go.

Clearly, capitalization can be confusing — especially if you take your cues from your reading material.

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For example, anyone who reads legal documents or marketing materials could be forgiven for thinking that the C is capitalized in “the company.” Businesses try to lay claim to any language that involves them, while the legal profession often uses capital letters to refer to people or entities on subsequent reference, like “hereinafter referred to as ‘the Company’ or ‘the Plaintiff.’” That doesn’t mean you should do the same. “Company” is just a plain-old generic noun, not a proper name, so you should leave it lowercase in most contexts.

Compass directions can be especially hard. In your reading, you probably see East and east in equal measure. So which is it? As you’ve probably guessed, it’s both.

AP Style calls for lowercase north, south, east, west, northeast and so on when you’re talking about compass directions. “Drive south for 3 miles.” But when you’re talking about a region, use a capital letter. “She’s from the South.” “Rain is expected in the Northeast.” “The firm will open a branch in the Midwest.”

Seems easy enough, until you start getting into the gray areas. For example, would you capitalize the W if you were talking about rain in the western/Western states? To me, it’s hardly clear whether you’re talking about a region or a compass direction. To AP, though, it’s a region: the Western states. But note: “He traveled from western Montana to southern Atlanta to Southern California.” The AP rule here says that you lowercase them when referring to areas of states or cities, but you make an exception for “widely known” sections like Southern California.

Titles are tough, too. “President Joe Biden is the president.” As a very rough guideline, you can follow AP’s rule of only capitalizing formal titles and only when they appear before someone’s name. So talking about the mayor without a name, it’s lowercase. We reelected the mayor. When talking about Mayor Morgan Jones, mayor is capitalized.

When the title is set off with commas, it’s not capitalized. So you’d write “He spoke with Vice President Kamala Harris” but also “He spoke with the vice president, Kamala Harris.”

It’s a little unclear what constitutes a formal title. For example, I’d have guessed that coach Chris Louis would use a capitalize c for coach. But AP says no. “Coach,” apparently, isn’t formal enough. But when you use it like a nickname, though, that’s different: Coach Chris. In that way it’s similar to “aunt” or “uncle.” When aunt or uncle part of a moniker, “Thank you, Aunt Carrie!” you’d capitalize it. Otherwise, don’t.

June Casagrande is the author of “The Joy of Syntax: A Simple Guide to All the Grammar You Know You Should Know.” She can be reached at JuneTCN@aol.com.

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